The present invention relates to prenyl methyl carbonate having the structure: ##STR3## and to novel compositions using such prenyl methyl carbonate to alter, modify, augment or enhance the flavor and/or aroma of foodstuffs, medicinal products, toothpastes, mouthwashes or chewing gum or impart flavor and/or aroma to said foodstuffs, medicinal products, toothpastes, mouthwashes or chewing gum.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors to (or in) foodstuffs, medicinal products, mouthwashes, toothpastes and/or chewing gum. These substances are used to diminish the use of natural material, some of which may be in short supply and to provide more uniform properties in the finished product.
Ethereal, solventy, ozoney, sweet, fruity, gooseberry, green, aniseed, licorice, floral and herbal aroma characteristics and ethereal, solventy, ozoney, sweet, fruity, gooseberry, green, spearmint, aniseed, licorice, floral and herbal flavor characteristics with cooling, "chloroform-like" effects and albedo-like flavor nuances are particularly desirable for uses in many foodstuff flavors, chewing gum flavors, mouthwash flavors, toothpaste flavors and medicinal product flavors.
The cyclic acetals of unsaturated aldehydes useful as such are described in U.S. Pat. No. 4,198,393 issued on Apr. 15, 1980, the specification for which is incorporated herein by reference. Methyl prenyl carbonate has never been indicated to be useful as such.
The prior art contains a large number of teachings regarding the use of organic carbonates in augmenting or enhancing the aroma of perfumes. Thus, U.S. Pat. No. 4,033,993 discloses the use of organic carbonates defined according to the structure: ##STR4## wherein R.sub.1 is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. U.S. Pat. No. 4,033,993 describes, for example, methyl-1-ethynycyclohexyl carbonate having a fruity, herbal complex odor and distinct fragrance of dill. In addition, U.S. Pat. No. 4,033,993 describes methyl cyclooctyl carbonate as having an herbal, natural and complex fragrance which is distinguished by a strong and long clinging flowery jasmine scent and further indicates its use in jasmine perfume compositions. U.S. Pat. No. 4,033,993 describes the preparation of the compounds defined according to the structure: ##STR5## according to the reaction: ##STR6## where R.sub.1 and R.sub.2 are defined as above.
In addition, U.S. Pat. No. 4,080,309 describes the perfume use of the carbonates defined according to the structure: ##STR7## wherein R.sub.1 ' is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 ' is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. Described in U.S. Pat. No. 4,080,309 are also such compounds as methyl cyclooctyl carbonate and the use thereof in jasmine perfume formulations. As is the case in U.S. Pat. No. 4,033,993, the carbonates of U.S. Pat. No. 4,080,309 are indicated to be prepared according to the reaction: ##STR8##
Geranyl ethyl carbonate is disclosed by Arctander "Perfume and Flavor Chemicals (Aroma Chemicals), Volume I" published in 1969 at monograph No. 1445 to have a "sweet and mellow, rosey and warm tenacious odor . . . sweeter than geraniol but not fruity like geranyl acetate, rather mellow in an almost musky way . . . ".
Geranyl methyl carbonate is disclosed for use in perfumery in co-pending application for U.S. Letters Patent Ser. No. 318,427 filed on Nov. 5, 1981.
Nothing in the prior art, however, discloses the prenyl methyl carbonate of our invention having the specific flavor nuances as set forth supra and having the specific flavor uses as set forth supra.
U.K. Patent Specification No. 1,336,787 and Canadian Issued Patent No. 935,174 disclose the production of methyl allyl carbonate by means of reaction of a trichloroacetic acid ester with a lower akanol. Nothing in either U.K. Patent Specification No. 1,336,787 or Canadian Letters Patent No. 935,174 discloses the compound methyl prenyl carbonate or the use thereof as a flavorant.